1912 – Ailes was born in Romney, West Virginia on May 25, 1912.
1929 – Attended and graduated from Episcopal High School in Alexandria, Virginia.
1933 – Attended and graduated from Princeton University.
1936 – Received his degree in law from West Virginia University and was admitted to the West Virginia Bar.
1937-1940 – Became Assistant Professor of Law in West Virginia University and married Helen Wales.
1940-1942 – Practiced his profession at Martinsburg.
1942-1946 – Became a member of the legal staff of the Office of Price Administration for two years.
1947 – Became a counsel to the American Economic Mission to Greece.
1948-1949 – Preceded the Truman Doctrine aid to Greece and Turkey. Returned to private law practice with the Washington firm of Steptoe & Johnson.
1951 – Became legal consultant to the director of the Office of Price Stabilization.
1961-1964 – Became Under Secretary of the Army from February 9, 1961 to January 28, 1964.
1964-1965 – Became Secretary of the Army from January 28, 1964 to July 1, 1965.
1966-1970 – Returned to legal practice and became director of the Panama Canal Company.
1971-1977 – Became President of the Association of American Railroads and resumed his career as a lawyer.
1985 – Ailes retired from the Steptoe and Johnson Law Firm.
2001 – Died in Bethesda, Maryland on June 30, 2001.